


In the Captain's Cabin

by my_soliloquy_chamber



Category: Assassin's Creed - All Media Types
Genre: Anal Fingering, Anal Sex, Assassin's Creed IV: Black Flag, Come Eating, Dirty Talk, F/M, Het, Oral Sex, Prostitution, Threesome - M/M/M, Vaginal Fingering, Vaginal Sex, mentions of bukkake
Language: English
Status: Completed
Published: 2020-09-16
Updated: 2020-09-23
Packaged: 2021-03-07 03:06:45
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 15,965
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26499838
Author URL: https://archiveofourown.org/users/my_soliloquy_chamber/pseuds/my_soliloquy_chamber
Summary: After many months at sea without so much as a whiff of a woman, Edward Kenway is finally back in Nassau, and he invites a woman into his cabin to help him play out all the fantasies he’s had during his lonely voyage.
Relationships: Edward Kenway/Original Female Character(s)
Comments: 4
Kudos: 15





	1. One - Nil

**Author's Note:**

> This story features two consenting adults, however, one of those adults is a prostitute which naturally muddles the defenition of consent a bit.  
> The setting is the early 18th century, which explains any unhygenic behaviour as they just didn't know any better.
> 
> This is going to get very explicit. Mind the tags.

* * *

  
Kenway opened the window at the back of his Captain’s Cabin and tossed out the remains of his bath. Placing the enamel bowl back on its side table, the folded the washcloth and hung it from the side to dry. Combing out his damp hair, he tied it back and walked over to his liquor stores. Pondering a bit, he chose a bottle of Madeira wine and carried it and two glasses over to his desk. He poured the wine and sat down in his comfortable wingback chair, the velvety upholstery soft against his naked backside. Sipping his wine slowly, he sat and stared at the door.

* * *

They had finally pulled into port after many long months at sea. The few times they had made landfall on a small pirate-friendly island, events had conspired to prevent him from bedding a woman, and now that they were _finally_ back in Nassau, Kenway was going to make damn sure to fill his cup. He had sent word with his men to the Madam of the brothel, to send him one of her best girls. His instructions included that the girl was fully and thoroughly bathed before coming and to wear a simple, full length dress like the non-working ladies wore. 

He himself had bathed himself properly after months of not quite caring. Now his skin and hair and even breath was sweet and fresh. All that remained now was waiting for the girl to show up. Hearing a chorus of whistles and catcalls from outside on the docks, it seemed it would not be long now. A gentle stirring started in his loins.

* * *

A soft knock finally came and the door opened to let in the young woman. She looked around the cabin, searching for him and smiled when her eyes fell on him seated at the far table by the window. “Captain Kenway? Madame Angélique sent me as per your request.” She smiled again and gave a coquettish curtsy. 

He smiled back and lifted his glas in greeting. “Welcome to my ship, lass. I have some elaborate plans for us this evening that will take us all the way to morning to fulfill. I hope you are agreeable?”

“That I am, Captain. Where do you want to start?” She began walking towards him, but stopped when he lifted a hand and spoke.

“I’m glad to hear that, lass. But to make sure we understand each other from the start, I intend to have you every which way, several times over, and with very specific intentions as to where on and in your person my release ends up. I have no intention of hurting you, but I have been at sea for months and have grown… frustrated. So, do you understand?” 

“Yes, Captain Kenway, I do. And if I may, I am eager to welcome you back home.”

“Your payment for the night is on that table there, I trust it will suffice?” She barely glanced at the coin purse and waved a dismissive hand.

“Well then, now that’s out of the way, I want you to come over here and sit on my lap.”

She walked around the table to his chair and noted his fully naked state with a smirk. The young woman slid into his lap and he pulled her legs to dangle over the armrest, making her lean against his arm and chest. He handed her the other glass of wine and picked his own back up again. For a few minutes they sat in silence, sipping their wine, while he occasionally buried his nose in her hair, taking deep breaths.

He sighed deeply. “Women… I always love you, but now that I’ve been away and not seen so much as an old crone in the distance, just thinking about you makes my member hurt. All these months with all these men.. The sounds, the sight, the smell of them.” He put his glass down and stroked his hand down her leg. “I’m going to fuck you in a bit, lass. It’s going to be quick and rough, but I just have to get it out of my system so I can focus on your women parts properly after.” He pulled up her skirts, exposing her legs, running his rough, calloused palm high up her thigh. As he let his fingertips glide through her soft, downy curls she sighed happily and buried her face in his neck, mouthing kisses. He slid his fingers deeper, drawing them through her folds and up towards her clit. She was damp, but not yet quite wet enough for him to take her comfortably.

Pulling his hand away, he reached into the neckline of her dress and scooped out one of her soft, full breasts. Bending down, he took the nipple in his mouth and sucked hard. She gasped and bucked her hips. His hand returned to between her legs, letting his thumb press against her clit while two fingers rubbed against her opening, feeling for her wet to start flowing. He released her nipple, licking it with the broad of his tongue. Wet and glistening in the candlelight, it stood as hard and erect as his member poking at her backside through her skirt. He blew on it to see if he could make it pucker further, before bending down to take it into his mouth again. He pushed his two fingers into her at the same time, rubbing circles against her clit with his thumb. She arched and panted against his neck, high, soft and unmistakably _womanly_ moans bubbling up from her throat.

She was wetter now. Not as sopping as he was planning on getting her, but good enough for now. He pulled his hand away and released her nipple. Taking hold of her, he stood up and sat her on the edge of the desk in front of him. Pulling up her skirts to expose her, he stood between her legs and positioned himself at her entrance with his hand. He looked her in the eye as he pushed in, she looked back holding on to his shoulders. Pushing further, her eyes fluttered and her mouth fell open. Once all the way inside he ground his hips against her, making her moan. She wrapped her arms around his shoulders and buried her face in his neck. 

Muffled he heard her say “You are so big.”

“Yeah. Are you ready?” She nodded against him and he pulled out and slammed himself back in. Setting a punishing pace he chased down his first release of the night.

It didn’t take long. The small of her hair and neck, the feel of her one exposed breast, still wet with saliva, pressed against his chest, her arms around his back, fingers clutching tight, and her panting moans in his ear, rising in volume. He didn’t stand a chance. Feeling his release rise, he grabbed her buttocks tight, snapping his hips frantically, growling feral as he came inside of her.

_One_ , he thought to himself.

* * *


	2. Two - Three

**Summary for the Chapter:**

> “No, where were we?” He pulled her legs closed and pushed her skirts down. “Out at sea, all alone with all these men and no woman to keep me sane, I fantasized about what I would do with and to the woman at port.”

* * *

  
Still clutching the girl to himself, he caught his breath and felt himself softening inside her. After a moment, he pulled out and laid her down on the desk. Lifting her legs up, he set her heels on the edge of the desk, removing her shoes as he went. Dropping them to the floor, he heard a soft clink. Looking around, he spied the wineglass the girl had been holding, dropped in the heat of passion, but thankfully for his bare feet, unbroken. He scooped and his own glass up and put them out of harm's way on the windowsill. 

Sitting down in the chair he moved it closer to the desk and to his companion for the night. She was propped up on her elbows, looking at him, feet still propped up on the desk, exposing her fully. “Lay back down, lass. I aim to spend some time here between your legs. Might as well get comfortable.” Using his thumbs, he pulled her folds apart and looked at her. She was swallowed, ruddy, and wet. Just how he liked them. Spreading her wider, he watched his seed slowly sliding out of her and down to her little puckered rose. Reaching with his tongue, he licked at the milky rivulet, pushing lightly at the tight rim for a second before licking back up to her quim and pushing his tongue inside.

She was moaning and squirming under him, having not had the time to come while he pounded into her. Now she was sensitive and frustrated. He pushed his hands in under her, taking her soft, round buttocks in his hands, revelling in how lovely and plump they felt. His tongue still deep inside her, chasing the taste of his own release, he tried to position his nose to give her some friction. The attempt only seemed to frustrate her, so he pulled his tongue out and sealed his lips over her clit, sucking gently. Pulling one hand from her rump, he pushed two and then three fingers inside of her slick, wet quim.

Her moans rose in pitch and her hips undulated against his lips. He pulled both hands free and pushed her legs apart as wide as they would go. Lips still sealed over her clit, sucking harder, he kept going until she just started to come and replaced his lips with the heel of his hand, grinding against her clit through her release. As she panted and moaned, Kenway sat and watched her quim and little tight pucker spasm and clench around nothing. His cock stirred in his lap.

When her spasms died down, he licked a stripe from pucker to clit, making her whimper in weak protest. He stood up and leaned down over her body. “Good lass, that was lovely.” He smiled at her dazed expression and sucked her exposed nipple into his mouth for a second before tucking it back inside her dress. “Do you want to come sit on my lap again for a bit, and regain your senses?”

She nodded and smiled satedly. He lifted her up and into his lap, keeping her skirts pulled up high and her legs spread wide so he could stroke her folds gently as he held her. Leaning into her, he blew warm air over the soft skin in the hollow behind her ear, following with pressing gentle kisses down her neck. “I take it your regular customers don’t often make you come, do they, lass?”

She chuckled breathlessly and shook her head. “No, not often no, and not so strong. And I can’t say any of them have ever done it quite like _that_ before. You just sat there and stared!”

It was his turn to chuckle. “I told you I have missed women. And that was just a little one. I didn’t even have my tongue inside you at the end. Your poor, hungry little quim didn’t have anything to hold on to.” He dipped his fingers inside her slowly. “No, petal, tonight you will come with your tight quim clenched hard around my cock.” He pulled out his fingers and stroked them down to her puckered opening. Massaging the slick, wet fingers against the tight rim. “You will come with my cock buried deep in your backside.” With her head resting on his arm, she looked up at him with wide eyes. He pushed his fingers back into her quim. “You will come with my cock in your quim and my fingers hooked inside your arse.”

He pulled his fingers out and pushed one of them slowly but firmly into the puckered flesh, feeling it yield for his slick digit. Her eyes went a little wider and he bent down to kiss her. As he devoured her mouth, she squirmed against his hand, pushing down. He pushed the second finger in, and her breathing got heavier, air puffing out of her nose, mouth filled with his tongue.

Lifting his head, he looked down at her, a slight frown pulling at his brows. “Is this the first time someone’s been in here?”

She shook her head vehemently and undulated against his fingers. “No, it’s… ah… common, lots of men want to stick their...mmm… themselves in there.”

Kenway scissored his fingers inside her. “Ah… so, you like it? Feels good when they push their hard cocks inside your tight little arse?” She nodded, moaning, and bit her lip. “But they don’t let you come? Even when you like it so? Tut tut, how ungentlemanly of them.” She nodded again and bore down on his fingers. “Well, lass, unfortunately for you, this would be getting ahead of ourselves a bit. I have plans, remember?” 

He pulled his fingers out and popped them in his mouth, savouring the taste of her quim mingled with her backside. “No, where were we?” He pulled her legs closed and pushed her skirts down. “Out at sea, all alone with all these men and no woman to keep me sane, I fantasized about what I would do with and to the woman at port.” He gave her a kiss and held her a little tighter.

“I thought about fucking a woman, hard, rough, right here on this table. I thought about licking and sucking a quim until it flooded with warm, sweet, juice. I thought about sitting between her spread legs, watching her quim quiver and beckon me. I sat right here in this chair, stroking myself, thinking and imagining and coming all over myself. I think there are some splatters on the carpet too.” She laughed and pulled his head down for another kiss. He deepened the kiss for a few moments, sucking on the lovely, pliant girl’s tongue.

“I thought about walking off this ship, stalking through the streets until I found a _woman_ , and pushing her roughly against a wall, her cheek pressed into the rough planks, ripping her skirts up, and just fucking her right there in the street.” He nosed behind her ear and over her neck, licking and sucking the skin between his words.

“Oh, don’t misunderstand me. I didn’t fantasize about raping her. In my fantasy, she was just as hornery as me, willing, eager, happy to share my need and take my seed. But, I know things are not like that outside of a fantasy, but I was also worried that walking through town to the brothel would see me snap before I got there, pushing myself on some poor, unsuspecting lady. So, instead, I asked to have you sent here, to me.”

She pulled his face in for another kiss. “And I am very happy you did.”

“The feeling’s mutual, my pretty lass. Now, like my fantasy, I want to push you up against this wall, pull your skirts up and fuck you nice and hard. You just stand there and take me, but feel free to make all the lovely sounds you want.” He lifted her off his lap and walked her over to the wall. For a second they two of them stood there, still. Then he moved, quick and cat-like, grabbing her by the hips, turning her around and pushing her roughly into the wall. Her hands flew up to brace herself and stop her face hitting the wall. 

Kenway growled with pleasure, her hands were up but her face cheek was pressed to the wood. Just like his fantasy. He pushed his body into hers, trapping her in place. Murmuring in her ear about her lovely scent and curves, and about how he was going to take her and make her feel so good, he pulled her skirts up over her waist, exposing her buttocks. Placing a hand between her shoulder blades, he held her firm against the wall while his other hand caressed her buttocks and thighs. He slid his fingers up and stroked them through her wet, slick folds. Kicking her feet further apart, he pulled her hips back and pushed his cock deep into her quim, shocking a cry of pleasure from her lips.

In contrast with the roughness he’d shown when positioning her, his thrusts were slow. Pulling all the way out, until the tip rested just outside, and then slowly pushing all the way inside. A few more thrusts, then he leaned forward and nuzzled behind her ear. “You feel so good. And your buttocks are lovely, so soft and plump. I think I will spend some time enjoying them later.”

She pushed back into his thrusts and sighed contentedly. “I would not mind.”

He smiled and kissed her neck. “Now, I want you to hold up your skirts so they don’t get in my way.” She rearranged herself while Kenway kept thrusting lazily. One hand reaching back to hold her skirts, one arm braced across the wall, cheek still pressed into the wood.

Kenway hummed happily and leaned in again to lick the shell of the girl’s ear, making her shiver. “I’m going to take my hand off your back, but I don’t want you to move from this position. Promise?”

She glanced back at him, small smile dancing over her lips. “I promise.”

Both hands now free, he took hold of her hips and sped up his thrusts a little. Slightly more shallow now, the firm thrusts hitched the breaths of the young woman, and made Kenway breathe a little heavier as well. He slowed down and lengthened his thrusts again. Shifting his hands on her hips he pulled her buttocks and labia apart, giving himself an unobstructed view of his wet, hard, member moving in and out of her quim. He especially liked the sight of the flared head spreading her a bit wider before pulling free, and the way her quim seemed to cling to his slick, swollen, glands for just a moment before releasing him.

Much better than his fantasy. In it, he had imagined taking - fairly roughly - a woman in full view of everyone on the street. They would see his cock slamming in and out, hear their skin slapping against each other, hear her loud, screaming orgasm as he hammered his way inside and spent his release. In his fantasy it had been rough, messy, loud, and very public. But that was thought up by a very frustrated and deprived Kenway. Now that he had been allowed his release inside of her, had gotten to taste and touch her, he was sated enough to take his time to enjoy himself. No frantic rutting required.

She squirmed at his slow pace, pushing back to meet his thrusts, trying to give them more speed. “Are you getting frustrated, poppet? You want me to take you proper? Help you come again?” She moaned and nodded. “I understand, and I do want to take you proper and come too. But first, tell me what feels best for you. This?”

He sped up his thrusts, but shortened them so only his glands were popping in and out of her sweet, clinging, opening. Her breaths hitched up to a fast moaning pant, small mewling sounds spilling from her lips. “Well, you are clearly enjoying this.” She nodded and moaned out a breathy ‘yes’. “But how does that compare to this?”

He slowed his pace a bit and lengthened his strokes so that each thrust brought his member as deep as it could go, pressing the girl slightly forward. As he bottomed out, he rotated his hips against her, moving his buried member against her inner walls.

Her breathing became less hitched, her moans deeper, and she started to beg. “Please, fuck me. You feel so good.. Please! Please, more! Fuck. More, I need just… more, please fuck me.” Her pleading evaporated his desire to tease or take it slow. Taking a sturdy grip of her hips again, he set a proper pace and fucked her the way they both wanted. Her moaning litany changed from pleading to praise and encouragement. It was so good. The sweet, clean, feminine small of her skin and clothes, the mingled scent of their slick, wet, sexes, the feel of her quim clinging, yielding to his thrusting cock. He was not going to last long, despite having come so recently.

After a minute of thrusting, the girl’s pleading was back. “Please. I need… please, more. I want to come. You feel so good. Please.. More.”

“Oh, sweet lass, you sound delicious. I want to help you, I want to make you come, but unfortunately, with all your skirts, I can’t reach your sweet, little, clit.” She moaned with disappointment and hung her head. “But you like men playing with your rosy, puckered, little backside. How about I give you a finger or two to tie you over until I can help you out properly?”

“Yes! Yes, please! Fill me, I need… you feel so good.” Kenway popped a thumb in his mouth and wetted it thoroughly, then he brought it to her opening and pushed inside. He was rewarded with her moans deepening. He fucked her faster. His thumb slid inside of her all the way to the base and he twisted his hand so his palm was gripping her buttock, thumb moving to the side and spreading her opening a little. He sucked his other thumb into his mouth, getting it nice and wet, and pushed that inside alongside the first. She groaned and pushed back into him.

Mirroring the hold of his other hand, his palm gripped her buttock, and his two thumbs spread her hole open. Between them, he could glimpse the pink, glistening flesh of her insides. They both groaned loudly, and he fucked her harder, almost rutting against her, just to finish quickly so he could drop to his knees and stick his tongue inside her. Make her come. But her moaning was getting louder, and she was meeting his thrusts with the same, frantic, desperation as he was giving them. Then it happened, she came, clit untouched. Her quim squeezed his cock hard, milking him, and the strong muscles of her rim pulled hard on his thumbs, trying to rhythmically close. The feeling was divine and he toppled over the edge himself, spilling inside of her squeezeing quim. 

Still coming, he managed through sheer force of will to gain enough control to pull out of her quim and push the head of his spurting cock against her other, still spasming, hole. Using his thumbs, still hooked inside of her, he forced her opening just a little bit wider, desperate for some of his seed to land inside.

Finally, he was spent and his knees gave out, dropping him to the floor behind her. He rested his head against her thigh, regaining his breath and composure. Laughing quietly to himself he thought; ‘ _Two’_.

Looking up, he saw her sweet, rounded buttocks, and in between them streaks of his pearlescent seed. Her quim was wet and smeared with white, the wet reaching down to her inner thighs and dewing in her curls. “Are you alright?”

She responded, panting, breathless. “Yeah.”

“You’re looking absolutely filthy down here. All wet and messy, and covered in my seed. I’m going to lick you now, get you cleaned up. And I will make you come again.”

She let out a shaky breath. “Ok.” 

Placing his hands back on her buttocks, he squeezed the lush globes before pulling them apart. He could see his milky seed leaking out of her clearly now, a rivulet from her quim, threatening to fall to the floor, and a smaller trickle from her puckered rosebud. He swooped in to catch the come from her quim on his tongue. Licking deep and sucking at her slick folds, he chased the taste of himself on her skin. He licked at her clit and felt her thighs tremble.

Focusing back on chasing his seed, he moved back and up to her swollen, puckered, hole, slick and gleaming with his release. Kenway licked up her cleft thoroughly, lapping up all traces of her juices and his milk, and then returned to her rosebud. Pointing his tongue, he pushed it inside. The flavor was heavy and musky, much more potent then when he sucked it off his fingers. The taste of his own seed was in there too, and he chased it, licking at the walls and feeling them try to clamp down on his tongue.

He snuck a hand between her legs and rubbed his fingers against her clit. The soft moans from above got louder. He licked deeper, taking every last drop of himself until all that was left was her strong, musky flavor. She was moaning and panting and undulating her hips, trying to push into his fingers and mouth at the same time. Her tight opening wasn’t quite as tight anymore, and was almost as wet and slick as her quim from from his saliva. Pulling his tongue out, he left wet, sucking kisses around the rim, before pulling away.

Kenway crawled in between her legs and turned around, sitting under her skirt, leaning against the wall. He pulled her hips closer and licked at her clit. Wrapping one arm up around her lower back, to keep her steady, he moved his other hand to her wet, empty, sex. Pushing two, then three fingers into her quim, he pumped them in and out while giving her clit light licks with his tongue. When his fingers were thoroughly wet, he moved them to her backside and worked them inside one by one. Once they were all securely inside her, he pushed his thumb into her quim and sealed his lips over her clit. He sucked and licked at her while pushing his fingers in as deep as they would go. The girl’s moans had escalated to screams of pleasure, and she was grinding herself down onto his face, almost putting her full weight on him, chasing her pleasure.

No one on the ship, or the docks, or the neighbouring ships moored close by could miss what was happening inside the cabin, and how much his lovely companion was enjoying herself. He chuckled and hummed against her clit, and the resulting vibrations finished her off. Her quim and tight pucker squeezed his fingers hard and her clit pulsed and swelled further on his tongue. Her loud screams died down to whimpers and a hand on his head through her skirts told him to ease off her sensitive clit.

Kenway loosened his grip around her back and helped her slide down into his lap, fingers still buried deep inside. Fighting against the skirts over his face with his free hand, his hair mussed and pulled from the tie, he managed to push them down between their bodies, to see her face. She was beautiful. Her face red and patchy, her hair a messy halo, her lower lip showing a deep divot where she had bitten down. Her gaze was a bit dazed and unfocused, mouth open, still sucking in steadying breaths. He leaned in for a soft kiss, and murmured against her lips. “Happy?”

She chuckled and pressed their lips together. “Yeah. Happy.” Her hands came up and stroked his hair back out of his face and retied his ponytail.

He wiggled his fingers inside her, making her squirm. “You know I’m going to have to take you here, next? Your reactions are simply too good to ignore.”

She looked into his eyes, face serious. “I **_really_** want you to do that. But… I’m going to need a bit of a rest first, I think.”

He laughed and kissed her again. “You and me both, poppet.”

* * *


	3. Three - Four

**Summary for the Chapter:**

> He pulled her tighter to his chest, her head resting on his shoulder.
> 
> They sat in silence, listening to each other’s breathing and the muffled sounds from outside. Eventually, their eyes slid shut and their breathing became slow and steady in sleep.

* * *

  
Kenway pulled his fingers out of the young woman’s body and they both got to their feet, unsteadily. He led her back to the chair and sat her down. He went about the cabin, collecting things and putting them on the desk in front of her, all the while sucking absently on his fingers.

“You really like the taste of women, don’t you?” She was watching him move about the room and glanced at the fingers in his mouth when he turned to look at her questioningly.

Smiling, he popped the fingers out. “I do, yes, very much. I like the taste of men too, but I’ve had enough of them for a while.” He returned to stand by the chair, taking their wine glasses from the windowsill and refilling them, handing one to her.

“So you lads, ah, help each other out while at sea?” She was clearly curious, but tried to hide it and took a drink from her wine.

Kenway pulled a washcloth from a bowl on the desk and wrung it out. With the damp cloth he wiped his member and pubic hair clean of their coupling. Returning the cloth to the bowl, he rinsed it and wrung it out again. “We do “help each other out” sometimes, yes.” He kneeled in front of her and lifted her skirts up. Urging her hips closer to the edge of the chair, he wiped her quim, her cleft, her pubic hair, and her inner thighs clean of their tryst.

“Some are enthusiastic and throw themselves into “helping” as soon as we leave shore. Some hold off longer, keeping to their own hand for some weeks or months until the loneliness and desire for companionship becomes too much.” He finished with her and stood up, dropping the cloth into the water again, and again rinsing it out. “Those men usually don’t mind sharing “help” with other men when out of options, but prefer women “helping” them.”

He wiped at his face with the damp cloth, scrubbing their residue from his beard. “Some men never want to give or accept “help” from other men, which is fine. Most of them take care of themselves and don’t mind or care what the rest of the crew might be getting up to when “helping”. However, some seem to get bitter and angry, judging and disparaging the other men for willingly “helping”. These men have a tendency to look down on and disrespect a Captain who gives or receives “help”. And sometimes, strangely, these men will force themselves on others, despite so vilifying the practice.”

He rinsed the cloth in the bowl and wrung it out again, before picking up the bowl and throwing the contents out of the window. Placing the bowl back on its side table, he folded up the washcloth and hung it from the edge. “Obviously, these are not good men to have on your crew, and luckily, I haven’t had the misfortune to have one on mine for a long while. Back at the desk he picked up a small knife and began to peel and slice oranges and guava into manageable pieces.

“And what kind of “help” do you, as the Captain, partake in?”

He glanced at her and gave a small smile. “Well, as the Captain, it’s generally not a good idea to be subservient or submit to the crew, but as you’ve noted, I like to taste.. So if one of my crewmen show themselves willing, I may indulge in taking their backside and then licking out my release, like I have with you. Or “help” them release directly into my mouth.”

She shifted in her seat and drank more wine. “You never, ah, you never let them take your backside?” She blushed brightly.

Kenway finished with the fruit, tossing the scraps out of the window, and placed the bowl within easy reach of the chair. He picked up the young woman and sat down with her in his lap. Picking up an orange slice, he fed it to her before taking his own. “The idea of me letting a man fuck my arse seems to excite you, lass. Why is that?” He popped a piece of guava onto his mouth before moving the bowl of fruit to rest in the girl’s lap, and picked up his own wine glass for a sip.

“I heard it feels better for men than for women. To do that, to take it.”

He opened his mouth expectantly and she fed him a piece of fruit before taking one herself. “And who have you heard that from?”

“The other girls. They say it’s different, better for men. That’s why they want to do it with the girls. They say the men just don’t understand that it’s just unpleasant or painful for women.”

“It’s not unpleasant for you, though.”

She blushed and fed him another piece of fruit before continuing. “No, it’s not unpleasant for me. Well, it is if there’s no warning or preparation, then it’s terribly painful and uncomfortable. But that doesn’t happen much. Most men are happy to help me prepare or watch me do it myself.”

At the thought of the young woman in his lap with her fingers deep inside herself, Kenway’s poor, spent, cock tried valiantly to spasm into life, but failed. It was too soon.

“I think maybe I’m built different from other women, liking things I shouldn’t.”

“Ah, lass, don’t say ‘shouldn’t’. You _should_ be allowed to enjoy yourself and take pleasure from the men who take their pleasure from you. Surely, the alternative is worse?”

She shrugged and nodded, and ate more fruit. “Yeah, you are right... But you don’t like it? Taking it like that?”

Kenway drank some wine and pondered. “I have “taken” a few times, but found I didn’t quite enjoy it the way I enjoyed doing the taking. But it depends an awful lot on who, and where, and of course, as you say, the preparation.” She fed him more fruit. “I do know about the notion that men may like it better than women though. There’s something inside a man’s backside that isn’t inside a woman, and rubbing that feels very good. Perhaps when you were new, the older girls told you to rub the skin behind a man’s sack while you take him in your mouth? It’s because you then rub that thing found inside his channel.”

She drank the last of her wine and fed him the last piece of fruit, reaching over to place glass and bowl on the desk. “Maybe I have that thing inside me too, and that’s why I enjoy it when the other girls don’t.”

Kenway laughed heartily and drained his glass, setting it, too, on the desk. “I will admit you enjoy me playing with your tight little rosebud more than any other woman I’ve had like that, and more than some of the men I’ve had too, but I doubt you have a piece of a man’s body inside of you. For one, I’ve explored around inside you and not found anything like that. But I promise to keep a lookout for anything unusual when I fuck you there, next.” She squirmed and sighed happily at his words. “Oh, are you ready for more, lass?”

She looked up at him with wide eyes. “Surely you can’t be ready again so soon?!” she exclaimed, almost alarmed.

He chuckled and shook his head. “Sadly, no, I will need a bit more of a rest. But if you are feeling a need, I’ll gladly lend you a helping hand.”

“Ah, no thank you. I feel the need to rest a bit longer as well.”

“Well, then, let’s rest and recuperate here together.” He pulled her tighter to his chest, her head resting on his shoulder. They sat in silence, listening to each other’s breathing and the muffled sounds from outside. Eventually, their eyes slid shut and their breathing became slow and steady in sleep.

  
  


* * *

Sometime later, the young woman stirred in his lap, and Kenway woke up. He stayed still, eyes closed to see what she would do, seemingly alone and unsupervised in his cabin. She lifted her head from his shoulder and turned her face into his neck, planting a soft kiss. When he didn’t stirr, she pressed her nose to his skin and took a deep breath. Putting her head back down on his shoulder, she stayed still for a few minutes. Then she slid carefully from his lap and stood up. He looked at her through his lashes, seeing her stretch her back and rub the back of her neck.

She turned back around to face him, and Kenway closed his eyes again. He felt her hand lightly on his cheek, and then felt her tuck a strand of his hair behind his ear. Hearing her feet pad softly over the floor, he slid his eyes open a sliver again. She was picking up her shoes from the floor and carrying them to the door. Putting them down there neatly, she walked back to the desk. Pouring herself a bit of wine, she sipped slowly while looking around at the different pieces of art and knicknacks scattered around the cabin. She finished her wine and stood holding the glass for a moment, before picking up his glass and the bottle, putting them on the windowsill, out of the way. She then picked up the empty fruit bowl and paring knife, and moved them to a side table.

She walked to the washbasin and picked up the still damp washcloth, wiping her hands and fingers thoroughly. Probably washing off the sticky fruit juice from their shared meal. She glanced at him and poured a small measure of water into the bowl, before picking it up and placing it on the desk softly. Soaking the washcloth and wringing it out, she turned towards him. He closed his eyes and waited. He felt her gently pick up his hand and wipe it clean, then moving to the other hand and cleaning that as well. She rinsed the washcloth and, mimicking Kenway, opened the window to toss the remaining water out. Putting the things away, she returned to the desk, and he closed his eyes again.

It was quiet for a moment, and he couldn’t guess what she was doing, but then he heard a gentle rustling of fabric and soft thumps on the floor by his feet. Her hands came to rest on his knees and pushed them apart a bit further. He felt the fabric of her dress against the inside of his thighs, against his pubic hair and soft member. She was kneeling between his legs and leaning in towards his body. He felt her fingertips gently trace the tattoos on his chest. After a few long moments, she slid her fingers down his stomach and then further down to his thighs, stroking the skin firmly with her palms. She moved out from between his thighs, her palms continuing to caress, down from the thighs, cupping the knees, sliding over his calves, and then up again to stroke his inner thighs.

He felt her fingers stroking his soft member and sack, before she leaned down and planted soft kisses over his sensitive skin. The kisses gradually became wetter and deeper until her tongue came out and licked his member, coating it with saliva. She pulled it into her mouth, sucking gently. Kenway decided to stop feigning sleep and opened his eyes. She was bent over him and did not notice his eyes open. Placing his hand on her hair, stroking it, he made her look up at him. She quirked a smile around the still soft member in her mouth. He smiled back at her and spoke, voice a little thick from sleep. “Suck **_hard_**.”

She raised her eyebrows but complied, and he felt the suction around his soft shaft increase dramatically and groaned loudly, his head thrown back. He pulled at her arms to stop her ministrations and get her up to straddle his lap, his shaft swelling a little beneath her. “Lovely wake up. Did you get bored all alone?”

She smiled and kissed his lips. “Yes, bored and lonely and in want of a helping hand… or cock, whichever’s on offer.”

“Little minx.” He kissed her deeply and savoured the feeling of having a lovely, willing woman in his lap. “I think it’s time to start peeling you out of this dress. I want to see and touch all of you.”

She reached behind herself to untie her lacing, but he stilled her hands and took over. Continuing their kiss, his hands worked to loosen her ties and allow the dress to be removed. Breaking the kiss to pull the dress up and off, he tossed it on the floor and looked at the girl in his lap. Her upper body was naked and exposed, but her legs still covered in a few layers of petticoats He cupped her breasts and thumbed the nipples. “Ah, breasts, how I’ve missed you.”

She laughed and stood on her knees, bringing her chest up to his face in clear invitation. Burying his face in her cleavage, he massaged her breasts and pushed them together into his face. He kissed and licked the skin, sucking red marks in a band of pearls from her sternum to her left nipple. Here he licked the delectable nub and sucked it into his mouth. One hand at her back kept her steady when she threw her head back and moaned. His other hand massaged the right breasts, lightly squeezing the nipple.

He sucked and licked at her left nipple for a long time, and when he finally lifted his head, the little nub was decidedly larger than its sister. Sucking red marks in a path to the right breast, he took the nipple into his mouth, tugging at it a little with his teeth before sucking hard. Her hands clutched his head to her chest and he released her back and made his way underneath her skirts to cup her buttocks. Skimming his fingers, he felt the outer edges of her quim already wet and dragged two fingers through her slippery folds, painting the slick backwards to her puckered rose. Dipping his fingers into her quim, he got them thoroughly wet and brought to massage and push at her tight opening. Her body yielded quickly and his fingers slipped inside. With his other hand, he pushed three fingers into her quim and pressed his thumb against her clit. He focused on circling his thumb and sucking on the hard, swollen, nipple in his mouth, letting her ride his finger at her leisure.

For what he had planned next, he wanted her loose and relaxed, and making her come would achieve that nicely. 

She began whimpering and moaning above him, still sensitive and ready to come. Her breaths panting out, harsh, as she clutched his head tighter and ground down harder on his fingers, against his thumb. She came quickly, not a big screaming one, but enough to relax her body and make her muscles pliant. Releasing his head, she sank down in his lap, legs and buttocks spreading wider, her forehead against his chest. Her nipple pulled out of his mouth as she sank down, and he wanted to pull her back up and bury his face back into her mounds, but he refrained. Instead he pulled his fingers out of her body and took hold of her waist, lifting her off his lap to stand on the floor.

Undoing the ties on her petticoats, he pulled them all off her, until she was finally standing as naked and bare before him as he had been all along. Stroking his palms over the soft skin of her stomach and around to her hips and back, he pulled her body to his and relished the feeling of their skin pressing together. “I’m going to bend you over this desk and stretch your tight, puckered rose with my fingers until you are open and relaxed and ready for me.”

She moaned, “Oh god, yes, please.” and spun around to bend over the desk.

He grabbed her hips and lifted her body up higher on the flat surface, only her tippy toes touching the floor. “Reach back and hold yourself open.” She complied, clutching her round buttocks. Kenway pulled out a stoppered vial from a drawer and poured a measure out at the top of her cleft. “Coconut oil.” He supplied at her questioning glance backward. He poured some into his palm and coated his fingers generously. Dragging his fingers through her cleft, he spread and massaged in the oil. Pushing against her opening with one finger had it slipping inside without resistance. Of course.

He moved it in and out a few times and added the second finger. Thrusting them too inside of her for a moment, and then scissoring them gently. Adding a third finger, he pushed them in, spreading them wide. Her breathing became deeper. He kept thrusting and spreading until her opening felt relaxed and loose and welcoming. Pushing his fingers in deep one last time, he pulled them free. She moaned a protest at the loss.

He poured more oil into his palm and stroked it over his hard member, coating it with slick. Grabbing onto his cock, he brought it to her loosened opening, watching it slip and slide in her oiled cleft. “Are you ready?”

“ _Yesss_.” She practically hissed out her reply and tried to spread her cheeks wider. Kenway pushed and felt himself sinking inside smoothly. She moaned low and long, and gripped her buttocks impossibly tighter, fingers digging deep into the flesh. He pushed all the way inside and ground his hips against hers. Pulling out slowly, he marveled at the sight of his long member sliding out of her smooth passage, glistening with oil. The bulbous head slipped out and she gave a small gasp. He pushed inside again, all the way, and moved to unclench her fingers from her buttocks. 

His rough palms massaged the plump cheeks, soothing the dark bruises left by her clutching fingers. Then he took hold of her hips and started thrusting at a firm, languid, pace. The feel of her velvet walls against his member was exquisite, but what made the moment divine was the girl’s reaction. Her moans had shifted to guttural groans from deep in her chest. She was trying and failing to get enough purchase on the floor to push back into his thrusts. He sped up, feeling his sack slap against her wet quim with each thrust.

Her groans mingled with sobs of “Yes, deeper, harder, more.” She was primal, animal, in her reaction and Kenway found himself growling in response. But it wasn’t enough. Even though he had fantasized about sodomizing a woman bent over his desk - of course he had - but now this wasn’t enough, not with her. He pulled out, hearing her frustrated protest, and lifted her off the desk. Sitting down in his chair, he pulled her to sit with him, lining his cock up with her opening as she sank down.

He lifted her legs and hung each over an armrest, spreading her wide and sinking himself deeper. His face buried in her neck, sucking bruising kisses into the skin, and his hands cupped and squeezed her breasts. All the while he thrust himself up into her, hearing her primal groans. He slid one hand over her soft stomach down to her sopping wet quim. Three fingers slid easily inside and he felt his own member through the thin wall. His thumb pushed against her clit, rubbing it firmly, and the beautiful, wild creature in his arms got louder.

She grabbed hold of the armrests and pushed her hips up before slamming herself down harder on his cock. With his enthusiastic help, she drove herself down and down and down on his cock until she screamed, head thrown back into his shoulder, back arched and arse pressed hard into his lap. Her holes spasmed harder than during her last screaming orgasm, squeezing his fingers and member like a vice. Finishing, she collapsed onto him, limp and still. Her breathing was deep and even, and he realized she had fainted.

Laughing, he spoke to the sleeping girl. “Well, lass, you certainly know how to make a man feel like a titan of sex.” He pulled his fingers out of her quim and sucked them clean. Jostling her head a little with his shoulder to rouse her, he smoothed his palms over her skin from her neck down to her legs, enjoying the feel of her body.

Coming around, she pushed her face into this neck, sucking kisses. “That was amazing, I’ve _never_ felt that way before.” She brought her arms up behind her head and wrapped them around his neck.

“Yes, you did certainly enjoy that. But I’m still in here, poppet. Hard and aching for release. Are you ready?” He jerked his hips, moving his member inside of her.

His movement made her gasp and whine. “I.. ah.. Please don’t.”

Kenway stopped moving. “It hurts?”

“Yes, a bit. I’m just tender there, we can…”

He cut her off. “Let me see.” Lifting her hips gently off his member, he heard her gasp and hiss as he pulled free. Still holding tight to her hips, he stood up and turned them around, placing her, kneeling, in the chair. He dropped to his knees behind her and spread her cheeks with gentle fingers.

Her rim was very swollen and an angry shade of red, but he could see no signs of tearing or blood. Rubbing her buttocks soothingly, he stood back up. “No injuries. I think you just got a bit too enthusiastic there at the end.”

She turned around in the chair, kneeling to face him. “You are very sweet, you know that?” Glancing to his hard member, not having softened much during this little interim. “But you are still hard and aching, and we really do need to take care of that, don’t we?” She smiled up at him and licked her lips.

He laughed and bent down to kiss her. “If you are offering, who am I to say no?”

“Just let me…” She climbed off the chair and grabbed the wine bottle from the windowsill. Her lips wrapped around the rim and he saw her take several long swallows before holding it out to him and wiping at her mouth with the back of her hand. “I was just so parched.” 

He drained the rest of the bottle and put it back in the window. “No wonder with all your screaming, lass.”

She went to sit in the chair, stopped just before lowering herself down. “Oh, I’m going to leave a big stain if I sit here. I’m still all wet.” He growled and grabbed her for a deep kiss. Pushing her down into the chair, he pushed at her knees to spread her legs - and her folds - wider.

Seated, her face was mere inches from his hard member. He thrust his hips forward, and the head bumped into her nose and slid to the side, leaving a wet streak across her cheek. She took hold of him and lapped at the head before taking him into her mouth and sucking hard. He gasped, hips jerking and she took him in further, until her nose was buried in his curls. Her tongue undulated against his cock, making him moan. She pulled off and looked up at him. “You were so close to finishing in my backside before, so there’s no need to go all slow and teasing now, is there? Just fuck me like you want to, I promise I can handle it.”

She engulfed him again, putting her hands on his hips and jerking him closer. He thrust his hips, sliding his cock in and out of her mouth, gently at first, and then hard, rougher. With every thrust he slipped deep into her throat, her nose bumping against his pubic bone each time. Her hands were fondling his sack gently, one finger behind it, rubbing against that spot that make men feel good inside. He was thrusting fast, feeling that tightening in his sack, when her hands came up to his hips, pushing him away. Reluctantly, he stopped and pulled free from her mouth.

“Switch.” She was standing up out of the chair and maneuvering him around to sit. He sat down and felt the wet cushion beneath him. She sure wasn’t wrong about leaving a stain. Falling to her knees in front of him, the girl pushed his knees wide and dove back in. Her hand wrapped around his shaft and her mouth sucked and bobbed fast, trying to make him explode. She got her wish, and he spurted into her mouth with a groan, clutching her head tight. Her sucking kept up until he pushed her away, panting and leaning back in the chair. Smiling to himself, he thought ‘ _Three_ ’.

The girl scrambled on top of him, and before he could react sealed her lips to his, letting his release spill into his mouth. He groaned in surprise and wrapped his arms around her, pulling her in tight, licking into her mouth and sucking on her tongue. They kissed deeply for a long time, caressing and enjoying each other’s bodies. 

Eventually they pulled apart, panting breaths, and she grinned wide. “Surprise! I didn’t want to deprive you, now that I know how much you enjoy tasting yourself.”

He chuckled and rearranged her on his lap, so her legs were dangling over the side of the chair again. “I do enjoy it very much, thank you.”

* * *


	4. Four - Six

**Summary for the Chapter:**

> Behind him, he could feel her step closer, her hands coming up to press against his shoulder blades. She trailed her fingertips gently over the inked lines, examining them closely. 
> 
> “Beautiful.” She breathed the word softly as her palms spread over his skin and caressed down over his back, and onward to cup and massage his buttocks. Her hands stroked lower to the backs of his thighs before her small, delicate hands slid in to caress the sensitive skin of his inner thighs, and up, her fingers trailing the cleft of his buttocks.

* * *

  
They sat silently, the girl tracing the tattoos on his chest and rubbing his nipples. “Your tattoos are beautiful, I’ve never seen any with so fine and clear lines.” She lifted his hand and traced the ink on his forearm, then slid her fingers up over his bicep, continuing further up to caress his clavicle, up his neck and over his cheek. “I wish you had a bed. I would love to lay you down and touch and taste you all over. Ride you and watch your face when you come.”

Hearing her words, he realized that despite her coming several times that night, her face had been hidden from him each time. 

“Where do you sleep, anyway?”

He gestured at a mess of ropes hanging from the ceiling. “Hammock.”

“Hmm, no, I’m not that adventurous.” She quipped, making him smile. She continued to explore his skin and tattoos, caressing her fingers over his shoulder, a soft hum escaping her lips as she skated over the portrait of Caroline, but she made no comment. Instead she lowered her head to his chest and pressed kisses to his sternum. He felt her palms press to his pectorals, massaging the firm muscles and thumbing his nipples. Her tongue sneaked out, giving his skin small kitten-licks, painting a wet trail to his nipple and sucking it gently.

She persisted in her exploration of his chest with her lips and tongue, speaking between the kisses. “I like the way your skin tastes. Just a little salt and sweat. It’s nice, not like… hm… well.”

He laughed and stroked her hair. “I did wash before you arrived, poppet. If I hadn’t, I would be tasting just as bad as your other patrons. And most of the time, I do taste like them. Not a lot of effort put towards washing and laundry at sea.”

She looked up at him. “Is that why you are naked? All your clothes are unwashed and smelly, cancelling out the bath?”

He laughed again and pulled her in for a kiss. “Yes, that is definitely part of it. But it’s also too warm to need clothes, and I didn’t feel like wasting time undressing once you had arrived.”

“But you kept my dress on for a long time. Why? You said you had missed women, wouldn’t a woman’s naked body help soothe that longing?”

He stroked his hands over her back, down to her buttocks, then around to her stomach and up to cup and fondle her breasts. “Clothed women are just as enticing. The dress hiding and hinting and teasing. Getting to lift up skirts and reveal hidden, forbidden skin. I especially like lifting up the back of a dress to expose legs and thighs, buttocks and a little glimpse of quim. I like that in the right dress and circumstances it can be lifted so that the girl can still look prim and proper from the front, passersby not noticing anything amiss. All the while, I can have my palms cupping her bottom, my finger in her quim, even my tongue in her arse.” He pinched at her nipples, still swollen from his hard sucking, and then moved his hand down to cup her bottom. “I also like undressing you. It’s like opening a present.” He kissed her deep, massaging her buttocks, pulling them wide apart and then pushing them together, listening to the wet, sinful sound her slick folds made every time he pulled them apart.

After some minutes of kissing, and her wiggling to try to move his fingers to more interesting places, she pulled away. “Can I see the tattoos on your back?”

He raised an eyebrow, but nodded and released her. She climbed off his lap and waited for him to stand up and turn his back to her. Behind him, he could feel her step closer, her hands coming up to press against his shoulder blades. She trailed her fingertips gently over the inked lines, examining them closely. “Beautiful.” She breathed the word softly as her palms spread over his skin and caressed down over his back, and onward to cup and massage his buttocks. Her hands stroked lower to the backs of his thighs before her small, delicate hands slid in to caress the sensitive skin of his inner thighs, and up, her fingers trailing the cleft of his buttocks.

He turned around and pulled her close. “Hey now. Tonight is about me enjoying your womanly attributes. If you want to enjoy my manly attributes, you should be paying me.”

“Oh, Captain, I might just take you up on that someday.” She smiled and pulled his head down for a kiss. “So, what other fantasies have you had on your voyages that we can act out?”

“Well, let’s see.” He lifted her up to sit on the desk and stood between her legs, hands resting on her hips. “In my most desperate, frustrated, depraved moments, I fantasized about having a woman splayed naked, here on this desk.” He stepped out from between her legs and pushed her knees together before hooking an arm under them and lifting her fully onto the desk. Urging her to lay down, he ran his hands over her body. “But in that fantasy, we’re not alone. I had several of my best crewmen in her with us, helping.”

Her head came up slightly from the desk as she glanced at the door. “Oh? What kind of help?”

Kenway climbed onto the desk and straddled her hips. His hands played with her breasts. “We stood around this desk and spent ourselves onto my naked companion’s skin. Then I had her use her hands to smear the mess into her skin, her breasts, onto her lips, down between her legs. And when she was done I would lick and suck it all up.”

His hands slid down her body and splayed over her hips, thumbs stroking through her pubic hair. “Really? How many crewmen?”

“Oh, that depends on my depravity at the moment. Five, ten, all forty sometimes. Depends on how much come I wanted to see her covered in, how much I wanted to eat. When I was desperate enough to fantasize about gobbling up the release of my entire crew, I knew it was time to get some “help” and called one or two willing men in here, and ate their release instead.”

She undulated her hips and bit her lip. “There you go again, fantasizing about me with other men.”

She smiled and pushed her hips up again. “Can’t help it. It’s a compelling fantasy. Besides, now that I know you’re for sale, maybe I’ll pay not just to get to touch and play with your body, but to get to watch you take on another man.” He growled and scooted down her thighs, slipping a thumb into the top of the girl’s slit to rub against her clit. Her hips came up again.

“So, is your crew just outside, waiting to barge in on your signal?” He grinned down at her, feral, before softening into a smile. “No, there will be no other men tonight. But I still want to spend myself on your skin and lick it up.” He moved out of his straddle and kneeled next to her, to bring her legs up to bend and spread wide.

“Well, that sounds lovely to me. What do you want me to do?”

“Touch yourself. Rub your clit, plunge your fingers into your quim, pinch and squeeze your breasts. Make yourself come and paint your juices over your skin and lips.” Her eyes fluttered shut for a moment as her hips undulated, and her tongue came out to lick her lips.

Kenway kneeled between her spread legs and picked up the vial of coconut oil. He poured a little onto his palm and stroked himself. Having already come three times that night, he was still far from being fully hard, but between his oiled hand, and the wet dream about to unfold before him, he was confident he could spend himself again. In front of him, the girl was fondling her breasts, tugging at the nipples. Her eyes moved over his body and down to his stroking hand. She licked her lips again.

“Tell me about the men you called into your cabin to help you.”

He chuckled and watched her hand move down to her quim, fingers dragging through the wet folds. “Jules and Hugo. French. They are two of the more… enthusiastic men on the ship. The last time I asked for “help” before we came here, they came to my aid. Sitting on the desk in front of me, tugging at their members.” The young woman pushed two fingers into herself and caressed her stomach with the other hand. “Then Jules came and stood kneeling in the chair, pushing his cock in my face. I took it in my mouth, sucking hard, milking him.” She moaned, thrusting her fingers and her hips. 

“Hugo stood behind him, preparing Jules arse with oily fingers.” He reached out with his free hand and squeezed her breast, feeling his member slowly swelling in his hand. “Jules was pushing himself back onto Hugo’s fingers and thrusting forward deep into my throat.” The girl in front of him whined and pushed a third finger into herself, Kenway pulled at her nipple, watching her back arch. “Jules is like you. _Really_ likes his arse played with, so between Hugo’s fingers grinding into that spot inside, and his cock sliding in and out of my throat, he didn't last more than a couple of minutes.” Her free hand was now rubbing at her clit rapidly. He was stroking himself faster, soon completely hard. “Jules came into my throat and mouth. Tasted so good to me. Like water in the desert.”

Her breathing as fast and her fingers pumping in and out of her quim. He grabbed her wrist and pulled the fingers out. She looked up at him bewildered. “Paint yourself. Get your juices all over your breasts, your neck, your lips.” She lifted her hand and dragged her wet fingers over her lips and down over her neck. The other was sliding through her folds and into her quim, scooping up slick, sticky juices and bringing then up to her breast, smearing them around. She put one hand back down and plunged her fingers inside, spreading her legs wider to get deeper. Her other hand played with and pulled at her nipple, mirroring Kenwat on the other breast.

“Hugo pulled him off the chair and we put him on the floor, arse in the air. Hugo oiled my cock up and lined me up with Jules' stretched hole. He put a hand on my arse and pushed so I thrust right in deep and hard.” She bucked her hips and fucked herself harder with her fingers. He took his hand off her breast and reached down to fondle his sack. “While I fucked Jules’ arse, Hugo stood next to me and pushed his cock inside my mouth. We got a real nice rhythm going where I thrust into Jules and Hugo thrust into my mouth.” She was clutching hard at her breast, fingers digging into the skin. Her other hand pulled out of her quim and smeared slick over the breast Kenway had been holding. Her fingers dove down to scoop up more and paint it over her neck and collarbones. “The young men were in there with me because I was desperate, so I didn’t last long. I broke rhythm with Hugo and went fast, hard coming deep inside Jules.”

The girl’s fingers were down in her folds again, but instead of thrusting into her quim, she was pushing a finger into her arse. Kenway grabbed her hand again and pulled it away. “No. You are too swollen and sore. Stick to quim and clit.” She moaned in protest and rubbed her clit in frustration.

“Hugo pulled his cock out of my mouth and stroked himself fast until he spurted on Jules' backside and cleft. I dove right in and licked it all up, from his cheeks, his cleft, some had landed on the back of his sack. My seed hadn’t begun to leak out of him yet. We rearranged ourselves so Hugo was sitting in the chair with Jules kneeling in the lap. I was kneeling behind Jules with my tongue deep inside his arse, licking my come out.”

She had three fingers in her quim again and her other hand frantically rubbing her clit. She was moaning protests as she squirmed on the table. “I can’t… more. I need you.”

Kenway, still pumping at his member, leaned down over the girl, bracing himself on one hand, careful not to touch her. “Come. Come for me. Be a good girl and come, and I promise I will stick my tongue deep inside your sore, swollen arse and soothe your poor, bruised little rim.” She looked up at him, eyes wide. He could hear her fingers working her quim frantically, hear the wet, squelching sound she was making, and his member swelled and throbbed, painfully hard. “Good girl. Let your little rosebud heal and I promise I’ll come by and stuff you full of my cock. Take you really nice and slow, with lots of oil and stretching so you don’t bruise and get sore. Fill your pretty little hole all night til you scream so loud the windows shatter.”

She was breathing fast, eyes wide and fixed on his, teeth clamped into her lower lip. Then her eyes rolled into the back of her head and she moaned loud, hips bucking hard. He stared at her as she came. A look of ecstasy washing over her. Mouth open in an almost perfect O, eyes rolling, and her head lolling back and forth. When she came down, she pulled her hands up and stroked them absently over her chest and stomach. Kenway moved to kneel over her chest and stroked himself fast. In no time, ropes of milky white splattered over her breasts and neck. In his minds’ eye he saw several more cocks fling their come onto her chest and face, making his sack clench almost painfully and a little more come dribbled out. He let himself go and pitched forward onto his hands and knees, resting his forehead against hers, mindful not to touch his skin to hers.

He let out a chuckle and thought; ‘ _Four_ ’.

“What are you laughing about?” came the girl’s sated, blissed out voice from beneath. “That was fantastic.”

He crawled back to kneel between her spread legs. “Spread it, smear it, massage it in.” He watched as the young woman dragged her hands from her neck, down her chest and stomach. She rubbed the sticky seed thoroughly into her breasts before bringing one hand down to stroke over her inner thigh, and in between her folds, while she pressed the palm of her other hand to her mouth and smeared it, making her mouth look like a messy child’s.

Kenway took her hands in his and licked her palms and fingers clean. Leaning over her, he lapped at the smears on her stomach and dipped his tongue into her navel, chasing a milky pearl. Continuing upward, he licked broad stripes under her breasts and up in the valley between her lush sticky mounds. Turning to her left breast, he licked and sucked at the skin, avoiding the nipple until the mound was cleaned. He then took the soft, darker skin into his mouth, licking and sucking gently. When he felt the skin under his tongue begin to pucker up, he sucked harder. He was rewarded by a soft moan from the woman below him. Tugging sharply at the nipple with his teeth rewarded him with another moan, but he let go and licked his way up to her clavicle where some of his seed had pooled. Sucking it into his mouth, he began to feel heat low in his belly and wished he could get hard again right away.

Her neck was covered with his now drying release, and Kenway had to work a little to clean her up. Long licks and sucking kisses did the job, and the girl moaned and was clutching at the back of his head by the time he finished. Moving up to her face, he licked at her chin and cheeks to clean up the mess before taking her lips in a deep kiss. She sucked at his tongue and nipped at his lips, and clutched at his head when he tried to move away to finish his cleaning, so he stayed and kissed her for a few moments longer. He broke the kiss and moved down to her right breast. His come had mostly dried into her skin, and he licked and sucked hard making her gasp and arch beneath him. Her nipple was tight and hard when he pulled it into his mouth, and he reveled in the feel of it against his tongue. He nipped at it and tugged hard, making her groan and buck her hips.

He pushed up on his hands and knees and made her trade places with him. “Up. Straddle my face.” She complied and they did an awkward shuffle until he was flat on his back on the desk and the girl was kneeling above him, wet quim glistening invitingly. Grabbing onto her buttocks he guided her lower and sucked at the inside of her thigh where she had smeared some of his come. He pulled her down to sit on his face and pushed his tongue deep into her quim, tasting her.

He pulled her back so her clit was centered over his mouth. Three fingers went into her quim as he sealed his lips over her clit and sucked. She bucked, groaning and pressed more of her weight down on his face. Her moans were loud, but muffled by her thighs pressed to the sides of his face. He wiggled, thrust, and scissored his fingers inside her quim while sucking harder on her swollen, throbbing clit. She ground down on his face, hard and greedy, and pressing his lips uncomfortably against his teeth. He gripped her buttock hard with his free hand, letting his fingers push into the cleft near, but not on her tight rim, and added his pinky to the tree already deep in her quim. She screamed and jerked her hips against his face violently for what seemed like minutes before calming down and easing up on the pressure against his face.

Kenway pulled out his fingers and grabbed her hips to urge her off his face. He guided the exhausted, spent girl to lay down, pillowed on his chest. She complied and fell asleep in moments. He yawned and stroked one hand over her hair. It was very late, or maybe early, and she had been working him too hard for him to stay awake any longer. Stretched out on his desk, holding the girl to his chest, he drifted off to sleep.  
  


* * *


	5. Five - Seven

**Summary for the Chapter:**

> This time, Kenway woke up first, the hard surface of the desk too uncomfortable compared to his usual hammock. He estimated that several hours had passed since they fell asleep. Early morning light filtered through the window and most of the candles had burned out.

* * *

  
This time, Kenway woke up first, the hard surface of the desk too uncomfortable compared to his usual hammock. He estimated that several hours had passed since they fell asleep. Early morning light filtered through the window and most of the candles had burned out. The girl was sleeping soundly, pillowed on his chest, and he gently lifted her head and arm to slide out from under her. Their skin was stuck together uncomfortably, and even in the low light he could see crusty smears on her chest and neck. Evidently, he had not been as thorough licking her as he had thought. Walking over to the window, he opened it to let in fresh morning air, before replacing the spent candles, bringing light back into the cabin.

His stomach rumbled loudly, and his mouth felt uncomfortably dry and parched. Last night had been a marathon of exertion for him, spending himself four times in just a few hours. No wonder he was hungry and so exhausted he could sleep on top of his desk for hours. He glanced at the girl. If he was spent and wrung out, how must she feel? How many times had he driven her to her release? Five? No, six times. She’d even fainted from the force of it. Kenway smiled to himself. The Madam really had sent him her best girl. He doubted many of any of the other girls could have kept up with him tonight. And not just kept up, exceeded him.

Right, so, they needed food, they needed drink, and the lovely young woman needed a bath. He pulled on a pair of trousers and grabbed the sheet from the hammock, covering the girl before walking out of the cabin. The deck was empty of crew and he descended quickly to the lower decks. 

The cook was awake inside the galley, squinting at a parchment in the low light. “Mornin’ Sam. Whatcha’ got there?”

“Mornin’ Cap’n. Just listn’ the provisions we need to restock.”

“Ah, yes. Provisions. I’m in need of some myself just now.”

The cook grinned lewdly. “Aye, Cap’n. I reckon you’d be ravenous after a night like you’ve had.”

Kenway smirked back and picked through the stores of the small galley. “Oh, I’m not quite done yet. But my lovely companion and I are both ravenous for food, so we can continue our exercises.”

The cook cackled approvingly. “That’s the spirit, Cap’n. Well, if you’re provisioning for a lady, there are some small fruitcakes left from the French frigate we took last month. They should still be alright to eat.” He gestured at a covered basket on top of the shelves.

Kenway reached up and pulled it down, taking out a cake and sniffing it. “So, you’ve been holding out on us, Sam? Hiding cakes from your long suffering crew?”

Sam gave a small smile. “With honorable intentions, Cap’n, I assure you. Some of the lads have landmark birthdays coming up soon. Figured if we hadn’t made port by then, they could have little cake at least, to make the day feel special.”

Kenway was packing his bounty into a kitchen towel to carry back to his cabin. “You are good to us, Sam. Keepin’ track and taking care of us all.” He clapped the cook on the shoulder and walked back to his cabin.

* * *

Inside he saw that the girl had rolled onto her back, but was still sound asleep. He placed the provisions on the table and went to fetch their glasses from the windowsill. Silently thanking the previous captain of the ship for indulging in frivolities like china and wine glasses, he pulled out plates and set them on the table. Unpacking the kitchen towel, he pulled out bread, cheese, an orange, and the fruitcake. Slicing up the food, he prepared them each a plate, and went to his liquor cabinet. Another bottle of Madeira wine, and after a thought, some grog. He poured the wine, and after adding two tankards to the table, poured the grog as well. 

He walked over to the desk and looked at the girl, sleeping soundly. It was almost a shame to wake her, but their time together would be over soon, and he wanted to spend it enjoying her. Stroking a hand over her hair, he bent down and kissed her sleeping lips. She didn’t stir, so he moved down to her neck and nuzzled the soft skin. In the candle light he could clearly see the purple bruises he’d sucked into her neck the night before. Well, a few more wouldn’t hurt.

Pushing his lips against her pulse, he sucked and nipped at the skin. Her head moved, angling to present more of her neck to his lips. Lifting his lips from her skin, he spoke softly. “Time to wake up, lass. It’s morning.”

The girl’s eyes fluttered open and she gave a sleepy smile. He helped her to sit up, swinging her legs over the edge of the desk, watching as the sheet fell into her lap, exposing her breasts. She pulled him in for a kiss, wrapping her legs around his waist. Huffing out a breath of surprise, she broke the kiss. “You dressed?”

“Aye, lass, I did a bit. Didn’t want to scandalize my crew when I popped down to the galley for some provisions.” He gestured to the laden table and helped hop down from the desk. She walked over, wrapping the sheet around her body, tucking it in on itself in a complicated fashion that secured it over her chest and left her hands free, but her body covered.

Her eyes were a little wide when she turned to him. “You did this for me?”

“For us. I’m very hungry, and I can't imagine that you are anything but ravenous.” They sat down and tucked into their meal, both eating with gusto.

“So, what’s next? What grand finale has your fantasies cooked up for us?”

He grinned and ate a piece of orange. “Well, after we’ve eaten I’m going to bathe you. I left you absolutely filthy last night, and I aim to rectify that.” She blushed a little and glanced down at herself. “I also seem to recall promising to tongue your arse, so we still have that to do. Beyond that, I’m not sure, but I do want to do _something_. Do you have any requests or fantasies of your own we can realize?”

She smiled and drank deeply from her mug, as parched as he was. “That’s not a question I’ve ever been asked before. I’ll have to think on it for a bit. I’d like to request you keep your trousers on for a bit though.”

“Really? Are you relieved that I’m finally showing some modesty, hiding my shame?” He spread his legs wide, making the bulge of his sack and member more obvious. 

She laughed and winked. “No, it’s for the same reason you kept my dress on. Tantalising and teasing. To see a man’s hard member through his clothes is titillating. And to get to open them and have it spring out towards you like a happy puppy. Well... like you say. It’s like opening a present.”

He smirked and drained his mug. “You are confident you are going to get me hard again. After our exhausting night.”

She snorted and rolled her eyes. “You’ve been like an hornery schoolboy all night. Springing right back up every time I knock you down. And now you are going to bathe me and tongue my arse? Yes, Captain, I am confident you will harden.“

He laughed and stood up, walking over to the washbasin and picking up the pitcher next to it. “Finish up your meal and I’ll fetch some more water.”  
  


* * *

When he returned she was standing by the window, looking out and sipping her wine. She turned when he opened the door. “Pondering what you want to do?”

“Mmm…” She grinned and put her glass down on the windowsill. “Right now I’m just really looking forward to the bath. I’m feeling a bit… itchy.”

“I’m not surprised. Hop up on the desk and your personal bath attendant will be with you shortly.” She pulled off the sheet and sat on the desk while Kenway poured water into the washbasin and mixed in soap flakes, stirring until they dissolved. He carried the bowl over and sat it to the desk. Soaking and wringing the washcloth, he started with her face, wiping her skin with the damp cloth, taking extra care around her mouth.

Rinsing and wringing the washcloth repeatedly, he washed her neck, arms, breasts, stomach, thighs and legs. Urging her close to the edge of the desk and spreading her knees wide, he kneeled and took care to clean her pubic hair and folds. Standing back up, he had her hop down from the desk and turn around so he could wash her back. The washcloth slid over her shoulders, her back, and her round buttocks.

He tapped a finger at the top of her cleft. “Open.” She bent herself over the desk, widening her stance, and reached back to spread her cheeks. Kenway kneeled again, examining her closely. He dragged the washcloth through her cleft several times, firm everywhere but her rim. “You are still swollen and red back here, so we are going to have to be gentle and careful with you. But, even sore, you do deserve a good wash.” 

He covered one finger with the damp cloth and wiped at the rim, applying very slight pressure. Then, pointing his finger, he carefully screwed it and the cloth inside up to the first knuckle. She had started sighing and moaning softly when he began cleaning her rim, when he pushed inside her moans got a bit louder. Not a trace of discomfort in her response. Pulling out his finger and cloth, he stood up and patted her bottom. “Stay here.”

He soaked and wrung the cloth, and wiped at his own chest, crotch, and chest before picking up the bowl and tossing the water out the window. Pouring a fresh bowl of water, he rinsed the cloth again and wiped over his chest, crotch, and face one more time. Carrying the bowl back to the desk, he used the clean water as he stroked the cloth over her back and thighs, kneeling down he rubbed the cloth over her round cheeks, then he wiped at her folds and pubic hair through her legs. He then focused back on her cleft, wiping it thoroughly. Covering his finger with the cloth again, he pushed inside, listening to her moans and sighs. He pushed in further, up to the second knuckle, and twisted his finger around. Her breathing sped up and he felt her push back into him.

He pulled out and stood up. Turning her around, he lifted her back to sit on the desk. Rinsing and wringing the cloth, he wiped back up her body; legs, stomach, breasts, arms, neck, and face. Pecking at her lips, he took the bowl and threw out the water, putting it back on the side table. Returning to stand between her legs, he stepped in close, leaning down to hover his lips over hers, his palms caressing her inner thighs. “Well, lass, have you decided what you want?”

“Yes, please take my backside again.”

“No, poppet. I’ll give you my tongue like I promised, and maybe a finger, but I won’t fuck you there. You are still bruised and swollen.”

She sighed and took his face in her hands. “You are very sweet, Captain. But I am fine. I can take it. I want to take it. And I don’t mind being a little sore.”

He kissed her deeply and slid a hand to stroke through her folds. “Poppet, you are thinking with your quim. If I fuck you and leave you even more bruised and swollen than you are now, you may think that’s fine. But the next patron you have may also want your backside, and then you are going to get _hurt_.”

His fingers slid from the opening of her quim up to her clit, rubbing it and then sliding down again. “Why don’t you ponder what else you might want, while I tongue your hole, like I promised?” He kissed her again and pushed her back to lay on the desk. Lifting her legs, he put her feet up on the edge to spread her wide. Then he pulled at her hips a little so she hung off the edge slightly, and kneeled.

Hooking his thumbs in her cleft he pulled her cheeks apart, giving him full access to her rim. Before diving in, he licked through her folds, tasting the fresh slick coming in. Then he slid his tongue down and licked at her bruised, sore, swollen rim. He wanted to soothe and arouse her, taste her deeply, none of his own flavor this time, and he wanted to make her come one more time before she left his ship. His tongue swirled around the rim, pointing and pushing inside for a moment, then out and swirling again. The girl sighed and moaned softly, and he sucked kisses against her opening and licked up through her folds to her clit again. Sucking on it, savoring her panting breaths, felt her try to push closer, spreading her legs wider.

Kenway dove back down to her pucker and pushed inside. He wiggled his tongue, trying to stretch her gently, to get deeper. His hands holding her cleft open shifted on her cheeks, the palms held on and spread her, while his thumbs teased at the creases between her thighs and labia. He alternated between wiggling his tongue, trying to push as deep in as possible, and sucking at her opening. Her flavor was strong musk, delicious and addictive, and he pushed deeper for more. A fluttering movement in her folds made him look up and see her rubbing her clit with her fingers. Her wet quim was weeping, and a thin trickle of her slick juice was running down into her cleft, onto his lips and tongue, inside of her hole. He sucked and licked and wiggled, pushing deeper and deeper, and the deeper he got the more firmly his nose got planted in her quim. She was bucking her hips now, panting high, thin, moans, and pleads for more.

Then one of her hands came down and grabbed his head, pushing him in and holding him still. Her hips bucked wildly and her moans changed to strong, loud, calls of “Yes, yes, there, yes!”. Her legs came and wrapped around his head, trapping him in a dark, muffled space of nothing but her smell and taste and spasming, undulating flesh against his face.

It was heaven.

Finally, she unwrapped her legs and let go of his head, falling back limp on the desk. Kenway took big, gulping breaths of air and waited for the spots in his vision to fade. He stood up and looked at the young woman. Her button was off the desk and her legs were barely keeping her from falling to the floor. Lifting her up, he sat them down in the chair, and kissed her neck. “Enjoy yourself?”

“Mmhm.”

“Figured out what you want?”

“Mmm.” She reached up and wrapped her arms around his neck, pulling him in for a kiss. “When I came here, you first had me here, sitting on the desk. I’d like that again, but slower. It went so fast that time I hardly had a chance to enjoy it. And I’d like to finish with you inside me instead of… on display.”

“Well, that can certainly be arranged.” He captured her lips and wrapped his arms around her back, holding on as he stood up and set her back on the desk, standing between her legs. “Before we go further, you’re going to have to unwrap your present though.” He smirked and glanced down at his trousers. 

Putting on a coquettish, girly voice. “For me? Oh, you _shouldn’t_ have!” She smiled and reached out to cup and trace his erection through the fabric. “Whatever could it _be_?” She undid the fastenings and pulled down on the trousers. His hard member sprang out and bobbed in the space between them. “Oh! It’s a _cock_! My favorite! However did you know?”

They laughed and kissed while she pushed his trousers down his legs until they fell to his feet and he could step out of them. Wrapping her legs around his waist, she deepened the kiss. He could feel her wet quim against his member, and thrust lightly through the folds as they kissed. She broke away and looked down between their bodies to where his member lay, glistening, nestled in her curls. Reaching down, she guided it to her entrance and looked up to meet his eyes. “Nice and slow now. Let me feel you.”

Keeping their eyes locked, he pushed inside her. Once fully sheathed, he ground his hips deliberately, making her moan, before pulling out again. He continued like that, slowly in and out for several minutes, watching her pupils dilate and her breathing get heavier. Eventually, though, he needed more and hooked his arm under one of her legs, opening her wider, letting him in deeper. He didn’t speed up his strokes, but added a hard thrust at the end of every slide into her. The new movement jarred her body, making her breasts bounce. She used her leg wrapped around his bottom to help pull him in. Her hands came up, one held his cheek and the other rested on his shoulder.

Her breathing was heavy, panting, and every hard thrust pushed a gasping moan from her mouth. Releasing his cheek for a moment, she pulled his arm from her back and guided his hand down to her clit. She brought her own hand back up to cup his cheek, letting her thumb caress his lips. He opened his mouth and licked, inviting it inside where he sucked on it, while his fingers stroked her clit and his thrusts got shorter and harder.

She was gasping, moaning, getting closer and closer to her edge, but she was still staring into his eyes. “Don’t finish, please not yet. Let me come first.” She pushed out her words between panting moans.

He picked up his pace, thrusting deeper, rubbing faster, sucking harder. Her moans increased in pitch and volume, and he felt her start to clench around him. She tried valiantly to maintain eye contact, but as her release washed over her, her eyes rolled back and her head lolled. He watched, drinking it in, and clamped down hard on his own urge to come.

She regained control and locked eyes with him again. “Go on. Let me see.”   
  
In another situation, at another time, with another woman, he would have buried his face in her chest or neck and rutted, pounding hard into her to come, no thought but the chase of his release. But now, here, they had spun a strange cocoon of intimacy between them, and he wanted to give her what she asked for. To stare into her eyes as he came. His hips kept thrusting and he felt himself tightening for his release. As the first spurts of his seed escaped him, she let out a small gasp, and took his face in both hands. Like her, he fought to maintain eye contact as he came, groaning and moaning, mouth open and panting.

As his hips slowed and stilled, she sighed happily and pulled him close to nose at his neck, nuzzling the skin. His hands ran absently over her hair and back as his member softened and slipped out of her. She pulled back and kissed his lips before touching them with sticky fingers. “You want a last taste for the road, or should I keep it all for myself?” She had dipped her fingers inside herself and scooped out some of her release. He growled and sucked her fingers into his mouth, then he dropped to his knees and licked at her quim, keeping far away from her clit.

When he finished, he stood up and lifted her off the desk. “Oh, so you’re just going to take yours and leave me hanging, are ye?”

“Yup.” He licked his lips and smirked. “I want you to leave here a little frustrated.”

She snorted, and he smacked her bottom playfully. “Go pick up your dress and we’ll get to prim and proper again.”

She collected her petticoats and dress from the floor where he’d tossed them the night before, while Kenway pulled his trousers back on. Hanging the dress over the chair, she pulled the petticoats on and tied them in place at her waist. He picked up the dress and helped her into it, tightening the and tying the laces. She was smoothing and fixing her hair with her hands.

“Hmm… Despite our efforts, you do _not_ look prim and proper.”

“Oh?”

“No, you look like you spent all night being ravaged by an hornery lout. Or an animal.” He traced the bruises on her neck and clavicles that he’d made when sucking kisses into her skin.

“Well, I suppose that’s the price I pay for having such a lovely time. And, Captain? Just between you and me, I’m really not a prim and proper lady.”

He laughed and gave her a kiss. “No, I suppose not. Still… Do you want me to walk you back? Make sure no one presumes to take liberties?”

“You really are sweet, Captain. But no, you don’t need to walk me. It’s that magical time of morning when the night-drinkers are sleeping, and the morning-drinkers haven’t gotten sauced enough to be a nuisance. I will be fine.”

They walked towards the door, and Kenway reached out for the coin pouch on the table, handing it to her. She hesitated. “I feel like I shouldn’t take it. I enjoyed tonight just as much as you did.”

He smiled and pushed the pouch into her hands. “I know, but you will take it anyway. This is your livelihood.”

She gave a small smile and nodded, slipping into her shoes by the door. “Don’t forget your promise to come see me and have your way with my backside.”

Now Kenway snorted. “Have _your_ way, you mean?” She grinned. “I’ll remember. How could I not? And who shall I ask for when I want to have you again?”

She looked up at him, surprise flitting over her face as she realized that she had yet to introduce herself to the man who’s spent the last several hours having her every which way. “Belle. You ask for Belle whenever you want me.”

“Well, then. Belle, thank you for a truly spectacular evening.” He kissed her cheek.

“Oh, believe me, Captain. The pleasure was _all_ mine.”

Then she stepped out the door into the soft morning light, and Kenway was alone in his cabin again.  
  


* * *

**Notes for the Chapter:**

> Well, that's the end. I hope you enjoyed reading this story.


End file.
